Tetrabutylammonium Fluoride → 9-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-one

HRID 2209757Notes

Reaction equation

[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4](O)[C@H:2]1O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[CH:4]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 21 (3.0 g, 8.6 mmol) in dry tetrahydrofuran (THF) (65 ml), cooled in an ice-bath, was added a 1M solution of tetra-n-butylammonium fluoride in THF (34 ml, 34.0 mmol). The mixture was stirred at 0° C. for 30 minutes, and the solvent was evaporated under vacuum. The residue was purified by chromatography on a silica gel column using CHCl3 methanol (7:1) as the eluent. Concentration of the TLC purified fractions yielded 1.36 g (67%) of 8: mp >310° C. (methanol); 1H NMR (DMSO-d6) δ 3.56 (2H, d, J =2.6 Hz, 5'-H), 4.84 (2H, m, 4'-H and OH, collapses to a multiplet integrating to one proton after D20 exchange), 6.12 (1H, br d, J=5.7 Hz, 2'-H), 6.47 (1 H, br d, J=5.7 Hz, 3'-H), 6.90 (1H, m, 1'-H), 8.06 (1H, s, 8-H), 8.10 (1H, s, 2-H), 12.40 (1H, br s, NH).

Workup

customthe solvent was evaporated under vacuum
customThe residue was purified by chromatography on a silica gel column
customConcentration of the TLC purified fractions

Sources & evidence

ORD record: ord-af0c71be4a10494c8dcff4dfa45047d7
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455339

Reaction notes

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